Silicon Valley loves Cory Booker. That could be a problem for him.

The Stanford grad is traipsing into a very different fundraising environment when he arrives in Silicon Valley this weekend.

He is the intermittent faster, the Tim Ferriss podcaster, the first-generation tweeter, the startup founder, the college pal of Reid Hoffman and other Stanford graduates of the early ’90s who built the modern Internet.

If any Democratic presidential candidate has tapped into the Silicon Valley zeitgeist over their careers, it is Cory Booker. And in 2019, that could be as much a political liability as it is a financial asset.

Booker, long the darling of the tech industry and some of its marquee leaders, is traipsing into a transformed Silicon Valley when he touches down in town this weekend for his first fundraising trip here since he announced he was running for president. Friday lunch guests at the San Francisco home of David Shuh, Friday dinner guests at the 9,300-square-foot Piedmont home of Ali Partovi, and Saturday evening guests at the Atherton home of Gary Lauder (an heir to the Estée Lauder beauty empire) are paying up to $2,800 each to rub shoulders with Cory Booker.

Then again, most have probably met him before. The presidential candidate has collected half a million dollars from the internet industry over his five years in the Senate, from people like LinkedIn’s Hoffman, Salesforce’s Marc Benioff, Google’s Eric Schmidt, Emerson Collective founder Laurene Powell Jobs, and early Facebook exec Sean Parker.

Why? He is culturally of this place, donors say.

But times have changed, and Silicon Valley is no longer merely an ATM for Cory Booker.

Twitter is no longer primarily a place to find an elderly man snowtrapped in his home in Newark, like Booker once did — it is now also a cesspool of hate and misinformation. Mark Zuckerberg is no longer a hero brandishing a $100 million check in a well-meaning attempt to save Newark’s schools, like Booker once described him — he is a bogeyman who badly mishandled our last election and is now as divisive as any of the people running for president.

Silicon Valley is itself a minefield that in some ways sums up the broader political challenge for Booker in 2020: He’s running as a liberal on issues including tech regulation, but the progressive left holds him in suspicion — and he could face more as he begins to court tech money more openly.

Booker’s tightrope walk needs to capitalize on his decades of coziness with tech elites and corporate America while not offending the liberal base that has them in its crosshairs.

Cory Booker’s super PAC bind

Democrats have dramatically soured on Silicon Valley over the last year: They’re now about evenly split on whether social media companies are good for democracy, for instance. That’s a far cry from a decade ago, when Silicon Valley epitomized the modern, progressive, cool mores of Barack Obama’s Democratic Party.

Cory Booker thought it did, too. Now, he appears less sure.

“The problem we have right now in America,” he told Recode in 2017, “is it is a perversion of the free market where corporate villainy is reigning.”

To understand Booker’s love/hate relationship with Silicon Valley, look no further than how he’s handling the Bay Area’s most prominent outside group so far this primary: the super PAC set up by his Stanford classmate, Steve Phillips.

Phillips and I are sitting in a corner of The Battery, the posh hangout for the tech elite in San Francisco. Phillips isn’t in tech — he’s a lawyer by trade, and a political operative by practice — but he is a key Booker emissary to the world of tech’s mega wealthy.

He’s introduced Booker to the likes of billionaire Salesforce chief Democratic donor Marc Benioff (at Obama’s second inauguration) and to Google super-executive David Drummond. And while Phillips has his detractors in the Democratic fundraising world who think him more flash than substance, according to some Democratic sources, he’s got the ability to raise big money thanks to his marriage into the family of Herb Sandler, one of the Democratic Party’s biggest donors in recent cycles. He’s prioritized mobilization above persuasion, working on behalf of candidates of color like Obama, Stacey Abrams, and even Kamala Harris.

His new group, Dream United, isthe only candidate-specific super PAC up and running so far in the 2020 primary. Phillips claims $4 million in commitments to back Booker.

“[Booker] was seen as the senator of Silicon Valley”

“He was seen as the senator of Silicon Valley,” Phillips argued. “There’s this cultural connection that’s a little bit deeper with him.”

But here’s the thing: Just like Booker isn’t totally sure how he feels about Silicon Valley big money, one gets the sense that Booker isn’t totally sure how he feels about his old friend Steve Phillips, either.

Booker has predictably been asked about how he feels about an outside group that can take millions from billionaires — and his protestations have not been effusive. When asked last week specifically whether Phillips’s group should be shut down, he told reporters, “I urge anyone and everyone not to have super PACs in this race.” Of course, candidates can’t coordinate with super PACs, so Booker can’t issue instructions to them on how to spend the money — but he’s not exactly washing his hands of them, either.

One tech donor close with the New Jersey senator told me that the word he has gotten from inside the Booker operation is to not cooperate with Dream United. But it’s a hazy instruction, and maybe intentionally so: Booker’s looking for rhetorical cover in a political climate in which super PACs have transformed from a financial necessity into a public-relations vulnerability; Phillips has enough rhetorical cover, too, to claim he hasn’t been totally disavowed.

Phillips said the criticisms of his group are merely “political gamesmanship” and that other Democratic contenders are eagerly accepting max-out $2,800 checks — and “not from waitresses or bus drivers,” as Phillips put it. But Phillips said he doesn’t need Booker’s permission to do the organizing work he has long done in the black community, and that he’s not shutting anything down just because of the moment’s politics.

“The perception of what a super PAC is is a convenient bogeyman. I get that,” he said as he held court in The Battery, where it was hard not to notice that he was one of the only African Americans in the room. “But if there’s a rich person who wants to support black-voter mobilization in Georgia, Alabama, and Mississippi, why would I turn that down?”

Another possible super PAC donor, Los Angeles billionaire surgeon Gary Michelson, who got close with Booker, a fellow vegan, after the senator headlined an animal-welfare banquet in Los Angeles in late 2016, said he was eager for the campaign to clarify its position on the super PAC. Despite Phillips’s claim that Michelson is a financialsupporter of Dream United, Michelson told Recode he was willing to donate up to $1 million to the super PAC but had said he wouldn’t make any commitments until he got more information.

“You’re reading the same signals I’m reading. It’s going to have to be better than that,” said Michelson. “I’d have to make sure that this would not go against Cory’s interests or his wishes. I don’t want to hurt someone by helping him.”

Booker’s love affair with Silicon Valley

That, in many ways, sums up Booker’s bind: How can he tap Silicon Valley’s largesse without being caricatured as the candidate of the neoliberal rich?

“The internet happened — and it happened where he went to college at the time he went to college”

Take a look at Booker on policy that matters to tech: He was once a champion of education reform, the cause célèbre of tech donors, but has grown quieter on that issue over time. He has targeted wealthier families with higher taxes as part of a plan to give poor kids money and attack the racial wealth gap, but it’s not as extreme as the Alexandria Ocasio-Cortez wing of his party.

And while tech policy drives relatively few tech donors, he has similarly tried to walk a fine line.

“There are lots of politicians on both sides of the aisle that seem to welcome throwing punches at employers,” Carl Guardino, who has hosted fundraisers for Booker and is the head of the Silicon Valley Leadership Group, told Recode. “Cory Booker will never do that.”

But on the other, the politics of tech have changed drastically since Booker first joined Twitter a decade ago, and Booker has spent the last few years grappling with things he might have missed.

Booker has taken a more aggressive stance toward big tech than the unbridled reverence he expressed for it in his early years. On an episode of Recode Decode in 2017, he cast a glaring eye on Amazon, Google, and Facebook — companies that he has long wooed and, if things had played out differently, that he might’ve worked at.

Booker advocates in the Valley are hopeful that his new punchiness toward big tech will insulate him from critiques on the left that he is too close with the players here.

Look at Matt Stoller, a leading Washington voice against the monopoly power of companies like Facebook and Google. You’d expect him to rake Booker over the coals for being in bed with big tech. I did when I called him.

But nope.

“It’s reasonable to consider his relationships with people in Silicon Valley,” Stoller told me. “But he spoke out in 2017 when very few people did.”

Those relationships, though, run deep. In the eyes of many donors here, he is, in their words, “one of us.”

A Stanford man at the dawn of the internet

Booker’s love affair with Silicon Valley began three decades ago when he arrived as a freshman at Stanford. A year behind Hoffman and a year ahead of Peter Thiel, the backup tight end Cory Booker got a little lucky.

“The internet happened — and it happened where he went to college at the time he went to college,” said Gina Binachini, a college friend of Booker’s who is a longtime entrepreneur in the Valley.

Those Stanford connections paid off with introductions. Booker, bursting with potential and ambition, got to know venture capitalists like Lauder, Ron Conway, and Ted Schlein as he was building a national profile in Newark.

Schlein, who met Booker before he became mayor, told me that he’s introduced him to some CEOs out here and has held sessions for him to learn about different parts of tech. Schlein later hosted a fundraising event for Booker at the Rosewood, Silicon Valley’s see-and-be-seen hotel on Sand HIll Road.

And for a young, camera-loving, media-savvy politician, technologies like Twitter were catnip. In 2009, Binachini recalls Booker spending a day at LinkedIn under Hoffman’s tutelage, meeting executives from places like Apple and Facebook, drinking it all in. Now, when every Democratic politician has highly paid digital strategists who can turn Luddites into Snapchat sensations, it’s easy to forget how agile Booker was on these platforms when they were still young.

He was genuinely impressed with these people.

From green tech to social media: inspiring meetings today. Incredible Silicon Valley leaders who are literally changing/empowering the world

His tightness with the Valley has already given him one buzz-saw experience: Booker was actually a startup co-founder, at a video company called Waywire, and his role at the startup blew up into a controversy during his 2013 Senate race when opponents labeled it a conflict of interest. (Booker eventually donated his shares.) That experience drew him closer to the Valley, though, helping him appreciate just how hard it is to build a successful company, one person who worked with him at the time said.

But Booker’s posture toward Silicon Valley in those early years looks almost naive in the rearview mirror.

Take the now-famous story of how Booker convinced Mark Zuckerberg to invest $100 million into Newark schools in 2012. It was brokered through a venture capitalist, Marc Bodnick, the brother-in-law of Sheryl Sandberg, at the elite media-deals conference in Sun Valley, the so-called “summer camp for billionaires.” The Newark mayor and the Facebook chief found common ground on a walk that Idaho summer. Zuckerberg at that point had never been to Newark. The infusion of cash was announced with glitz and glam on the set of another billionaire, Oprah.

The project largely ended up a bust. So did Booker’s bet that a tech billionaire could throw enough money at a problem and fix it — a belief that sounds very quaint in 2019.

Still, all those those controversies, startup travails, Sun Valley visits, and reunions at his alma mater have given Booker a range of possible donors that are the envy of the Democratic field.

But the general sense gleaned from interviews with top Democratic givers and fundraisers in Silicon Valley is that the emphasis right now — above all else — is on a candidate who can win. Booker’s politics are more mainstream than the Elizabeth Warrens of the world, And tech donors, predictably, are technocratic, data-driven, and less convinced that the class warfare waged by the furthest-left candidates is a winning strategy.

“That is the single No. 1 important criterion. Consider the alternative,” said Lauder, Booker’s host this weekend. “If I didn’t think that Cory had a chance, I wouldn’t be doing this.”

It’s important not to overstate Booker’s immediate financial support. I reached out to about two dozen top Democratic donors and fundraisers in the Valley, including some who had backed Booker in previous races, and asked if they planned to endorse him this cycle. It’s hard to find committed donors right now.

Former eBay CEO John Donahoe, a top giver in recent cycles? He’s met with Booker and says he’s “impressed.” But an endorsement? “It’s way too early.”

Kleiner Perkins kingmaker John Doerr told me through a spokesperson, “It’s too early in the process for him to have a sense of who he will support.”

Even Schlein, Doerr’s partner at Kleiner Perkins who has known Booker since before he was mayor, said it’s “very early to endorse anyone yet.”

Silicon Valley’s big donors are torn. But do they even matter anymore?

It’s not a Booker-specific problem. Democratic donors across the country are generally pushing the brakes on early exclusive endorsements of candidates this cycle, in a jump-ball field and with the decisions of several donor-friendly candidates — like Beto O’Rourke, Joe Biden, and even Mike Bloomberg — still to be determined.

Facebook co-founder Dustin Moskovitz — the new hot money in Silicon Valley Democratic politics — is not expected to make any early endorsements in the primary. Hoffman, despite his decades-long relationship with Booker dating back to Stanford, is expected to write $2,800 checks to as many as six Democratic primary candidates but is not going to be using his billions to sway the process, according to a person close to him. That might surprise some Booker supporters who were hoping for Hoffman to advocate for him more publicly.

It is Kamala Harris, leading Democratic fundraisers in the Valley say, who represents the clearest challenge to Booker in the money world here. Her ties to Silicon Valley are less cultural than Booker’s and more rooted in organizational power as an incumbent senator and, before that, a Bay Area politician.

One early get was Susie Tompkins Buell, a close associate of Hillary Clinton and one of her top bundlers, who surprised the Silicon Valley setwith her early Harris endorsement this month. Harris is also close with Benioff, who has known her for 30 years, but he’s likely to back several candidates this cycle.

“Kamala is one of the highest-integrity people I’ve ever met and is a phenomenal prosecutor,” Benioff told me. “She is truly an impressive leader with a strong legal and public service background.”

Marc Benioff: “Kamala is one of the highest-integrity people I’ve ever met”

Another person making their preferences public: Ron Conway, a venture capitalist and an influential Democratic powerbroker, listed Harris and Booker as the two candidates he’s backing this cycle.

Booker and Harris “have the greatest understanding of Silicon Valley and have cultivated the deepest relationships,” Conway told me. “Though they won’t always agree with the tech sector’s perspective, they’re generally both allies and each ‘gets it.’”

But times have changed in an era in which Bernie Sanders can raise $6 million within 24 hours of his launch from small donors (more than Phillips has claimed, for instance). How deep the Moskovitzes and Hoffmans and Benioffs and Conways will give during the general election will matter to the nominee. But there is an ascendant belief in the world of Democratic money that the personal preferences of the bagmen matters less than it once did, especially in primaries.

While the well-networked bundler who can collect more max-out contributions will still be in demand, there are not many outside groups for Silicon Valley’s billionaires to back if they’re hoping to give beyond the $2,800 maximum campaigns can accept.

What Sanders showed two elections ago, and O’Rourke one election ago, is that Democrats can be competitive with big-money machines merely with good old-fashioned viral marketing.

“We used to have this invisible primary where reporters would closely follow fundraising numbers,” said Shomik Dutta, an Obama fundraiser who recently joined Harris’s national finance committee. “The first litmus test of strength is now content.”

That may be the biggest ego blow for donors meeting Cory Booker this weekend in Silicon Valley: They don’t matter like they once did.